I had a five-year plan. It lasted until a stack of brochures showed up.
It was a gorgeous autumn day in Toronto. The leaves were showing off, turning bright shades of yellow, orange, and crimson red. The crisp air didn’t bother them like it bothered me.
I’d recently graduated from law school. Yet, I had no idea what I wanted to do with my life… until that day.
Don’t get me wrong, law school opened many doors. But it was a career I fell into by default rather than design.
I spent the better part of that fateful morning reviewing a series of pamphlets I had been asked to consolidate. I poured over each one, neatly stacking them on my desk as I finished. Most importantly, I couldn’t take my eyes off them.
They talked about conflict.
Not the destructive kind that we see on social media and the news these days. You know what I’m talking about… the kind that makes you want to click, sigh, and type a comment you’ll regret by Thursday.
No, this was the “boring” kind of conflict: conflict resolution.
The kind where two people sit down together and have a true dialogue. Where communication means more than people saying “I hear you” and clearly not hearing a thing.
Before you scroll on, let me also share that I used to hate conflict. (This was, in hindsight, a questionable foundation for a career built on disagreeing for a living, but I digress.)
I had avoided confrontation my entire life.
And yet there I was, captivated. Who were these people who called themselves peacemakers*? How had they learned to do what seemed like the hardest thing in the world: helping people who are fighting to work together?
*Peacemaker: a person who sits between two people who each believe they’re the reasonable one, and somehow leaves with everyone still talking.
As much as I tried to ignore what I was feeling, I couldn’t seem to shake the inner tug to dig deeper.
It also made my shoulders tighten.
My career was finally shaping up, and the thought of throwing it all away felt irresponsible. The cautious part of me was terrified of failure. It had kept me safe for many years, like an umbrella I carried on perfectly sunny days. I never got wet. But I also never got to feel the sun.
I took a deep breath and Googled what it would be like to work in this area. The cautious one spoke up immediately:
You’re nowhere near as qualified as they are.
I haven’t applied for anything.
Yet… That’s what worries me.
This time another voice chimed in. It didn’t speak in words, but in sensations: a flash of excitement, deep fascination… and a mildly terrifying sense that my whole world was about to change.
I now know that this was the curious part of me.
Has this ever happened to you? The feeling of being pulled in two directions by different parts of yourself?
On that beautiful autumn day, the curious one gained enough courage to put the umbrella down. It looked the cautious one deeply in the eyes: “It doesn’t matter what you think we’re supposed to do… we need to keep going.”
I could feel the cautious one release its grip… almost as if it was waiting for someone to grab the steering wheel so it could finally step down for a while. My shoulders softened and just for a moment I stopped caring about mistakes, failure, or looking foolish. I simply felt the joy of wondering.
The next day, I went to a bookstore and bought a book on conflict resolution. One book became a stack, the stack became a shelf, and eventually the shelf became a career.
If you’re feeling torn, you may not have a decision to make so much as an internal meeting to chair. I recommend bringing patience, snacks, and low expectations for the first 30-minutes.
I never did go back to the five-year plan. I hear it’s waiting for an apology.

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